Tetra-kis[μ-4-(methyl-amino)-benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-N)zinc(II)] dihydrate.

The title mol-ecule, [Zn(2)(C(8)H(8)NO(2))(4)(C(10)H(14)N(2)O)(2)]·2H(2)O, is a centrosymmetric binuclear complex, with two Zn(II) ions [Zn⋯Zn' = 2.9301 (4) Å] bridged by four methyl-amino-benzoate (MAB) ligands. The four nearest O atoms around each Zn(II) ion form a distorted square-planar arrangement with the distorted square-pyramidal coordination completed by the pyridine N atom of the N,N-diethyl-nicotinamide (DENA) ligand. Each Zn(II) ion is displaced by 0.3519 (2) Å from the plane of the four O atoms, with an average Zn-O distance of 2.030 Å. The dihedral angles between carboxyl-ate groups and adjacent benzene rings are 10.57 (10) and 16.63 (12)°, while the benzene rings are oriented at a dihedral angle of 81.84 (5)°. The pyridine ring is oriented at dihedral angles of 40.49 (6) and 51.25 (6)° with respect to the benzene rings. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The π-π contact between the inversion-related pyridine rings [centroid-centroid distance = 3.633 (1) Å] may further stabilize the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶) and for the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1995 ▶, 2009 ▶); Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶).

Experimental

Crystal data

[Zn2(C8H8NO2)4(C10H14N2O)2]·2H2O

M = 1123.89

Monoclinic,

a = 10.1384 (2) Å

b = 25.6931 (3) Å

c = 10.5170 (4) Å

β = 103.061 (2)°

V = 2668.67 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.97 mm−1

T = 100 K

0.52 × 0.52 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.609, T max = 0.905

23512 measured reflections

6638 independent reflections

5562 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.02

6638 reflections

346 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040409/ci2912sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040409/ci2912Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn2(C8H8NO2)4(C10H14N2O)2]·2H2O	F(000) = 1176
Mr = 1123.89	Dx = 1.399 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8651 reflections
a = 10.1384 (2) Å	θ = 3.0–28.2°
b = 25.6931 (3) Å	µ = 0.97 mm−1
c = 10.5170 (4) Å	T = 100 K
β = 103.061 (2)°	Plate, colorless
V = 2668.67 (12) Å3	0.52 × 0.52 × 0.10 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	6638 independent reflections
Radiation source: fine-focus sealed tube	5562 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→10
Tmin = 0.609, Tmax = 0.905	k = −30→34
23512 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0383P)2 + 2.063P] where P = (Fo2 + 2Fc2)/3
6638 reflections	(Δ/σ)max = 0.001
346 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Zn1	−0.04338 (2)	−0.014479 (8)	0.118981 (18)	0.01584 (6)
O1	−0.20843 (14)	0.01538 (5)	−0.00434 (12)	0.0240 (3)
O2	0.14508 (13)	−0.04361 (5)	0.18309 (12)	0.0202 (3)
O3	0.03250 (15)	0.06111 (5)	0.13786 (14)	0.0268 (3)
O4	−0.09993 (14)	−0.08625 (5)	0.04128 (12)	0.0225 (3)
O5	−0.19322 (15)	0.13404 (5)	0.50417 (14)	0.0281 (3)
O6	0.95980 (18)	0.15202 (7)	0.75046 (18)	0.0397 (4)
H61	0.967 (4)	0.1239 (15)	0.808 (4)	0.087 (12)*
H62	0.904 (4)	0.1385 (15)	0.671 (4)	0.088 (13)*
N1	−0.12123 (15)	−0.00735 (6)	0.28204 (14)	0.0166 (3)
N2	−0.39214 (16)	0.12268 (6)	0.35808 (15)	0.0201 (3)
N3	−0.73560 (17)	0.14248 (7)	−0.25237 (16)	0.0279 (4)
H3A	−0.7889	0.1404	−0.1995	0.033*
N4	0.2505 (2)	0.28515 (7)	0.3274 (2)	0.0434 (5)
H4A	0.3067	0.3035	0.2962	0.052*
C1	−0.23030 (18)	0.03966 (7)	−0.11144 (16)	0.0168 (3)
C2	−0.36417 (18)	0.06493 (7)	−0.15463 (16)	0.0162 (3)
C3	−0.39620 (19)	0.09599 (7)	−0.26573 (17)	0.0194 (4)
H3	−0.3338	0.0997	−0.3178	0.023*
C4	−0.5190 (2)	0.12146 (7)	−0.29995 (17)	0.0217 (4)
H4	−0.5382	0.1421	−0.3744	0.026*
C5	−0.61546 (19)	0.11639 (7)	−0.22320 (17)	0.0204 (4)
C6	−0.58436 (19)	0.08385 (7)	−0.11255 (18)	0.0217 (4)
H6	−0.6477	0.0789	−0.0620	0.026*
C7	−0.46113 (19)	0.05944 (7)	−0.07914 (17)	0.0194 (4)
H7	−0.4413	0.0388	−0.0047	0.023*
C8	0.08144 (18)	0.09445 (7)	0.07307 (17)	0.0196 (4)
C9	0.1199 (2)	0.14569 (7)	0.13448 (17)	0.0212 (4)
C10	0.2042 (2)	0.17976 (7)	0.0866 (2)	0.0248 (4)
H10	0.2328	0.1713	0.0112	0.030*
C11	0.2458 (2)	0.22608 (8)	0.1502 (2)	0.0298 (4)
H11	0.3032	0.2481	0.1178	0.036*
C12	0.2017 (2)	0.24024 (8)	0.2638 (2)	0.0304 (5)
C13	0.1107 (2)	0.20754 (8)	0.3067 (2)	0.0321 (5)
H13	0.0755	0.2173	0.3776	0.038*
C14	0.0728 (2)	0.16080 (8)	0.24425 (19)	0.0274 (4)
H14	0.0147	0.1388	0.2758	0.033*
C15	−0.10860 (18)	−0.04226 (7)	0.37916 (16)	0.0170 (3)
H15	−0.0671	−0.0740	0.3710	0.020*
C16	−0.15508 (19)	−0.03269 (7)	0.49092 (17)	0.0195 (4)
H16	−0.1474	−0.0580	0.5555	0.023*
C17	−0.21321 (18)	0.01504 (7)	0.50527 (17)	0.0189 (3)
H17	−0.2428	0.0227	0.5807	0.023*
C18	−0.22681 (18)	0.05145 (7)	0.40509 (16)	0.0166 (3)
C19	−0.18061 (18)	0.03849 (7)	0.29495 (16)	0.0174 (3)
H19	−0.1911	0.0625	0.2272	0.021*
C20	−0.27156 (19)	0.10611 (7)	0.42525 (17)	0.0190 (4)
C21	−0.4910 (2)	0.09017 (8)	0.26852 (18)	0.0238 (4)
H21A	−0.4441	0.0615	0.2379	0.029*
H21B	−0.5342	0.1108	0.1933	0.029*
C22	−0.5985 (2)	0.06864 (9)	0.3335 (2)	0.0320 (5)
H22A	−0.6640	0.0495	0.2707	0.048*
H22B	−0.6426	0.0968	0.3672	0.048*
H22C	−0.5570	0.0460	0.4037	0.048*
C23	−0.4330 (2)	0.17653 (7)	0.3789 (2)	0.0264 (4)
H23A	−0.3975	0.1861	0.4695	0.032*
H23B	−0.5310	0.1784	0.3616	0.032*
C24	−0.3819 (3)	0.21482 (9)	0.2916 (3)	0.0398 (6)
H24A	−0.4139	0.2491	0.3050	0.060*
H24B	−0.4147	0.2049	0.2020	0.060*
H24C	−0.2847	0.2147	0.3124	0.060*
C25	−0.7761 (2)	0.17342 (9)	−0.3688 (2)	0.0345 (5)
H25A	−0.8664	0.1862	−0.3752	0.052*
H25B	−0.7740	0.1524	−0.4438	0.052*
H25C	−0.7151	0.2022	−0.3650	0.052*
C26	0.2125 (4)	0.30333 (9)	0.4443 (2)	0.0561 (8)
H26A	0.2589	0.3353	0.4726	0.084*
H26B	0.2368	0.2776	0.5118	0.084*
H26C	0.1165	0.3091	0.4261	0.084*

	U11	U22	U33	U12	U13	U23
Zn1	0.01825 (11)	0.01770 (11)	0.01276 (10)	0.00284 (8)	0.00601 (7)	0.00051 (7)
O1	0.0237 (7)	0.0314 (7)	0.0170 (6)	0.0086 (6)	0.0049 (5)	0.0050 (5)
O2	0.0183 (6)	0.0244 (7)	0.0186 (6)	0.0045 (5)	0.0054 (5)	0.0017 (5)
O3	0.0310 (8)	0.0206 (7)	0.0336 (7)	0.0001 (6)	0.0176 (6)	−0.0022 (6)
O4	0.0273 (7)	0.0194 (6)	0.0198 (6)	−0.0003 (5)	0.0036 (5)	−0.0022 (5)
O5	0.0265 (8)	0.0257 (7)	0.0314 (7)	−0.0034 (6)	0.0053 (6)	−0.0094 (6)
O6	0.0400 (10)	0.0393 (9)	0.0388 (9)	−0.0006 (8)	0.0065 (8)	0.0140 (8)
N1	0.0162 (7)	0.0194 (7)	0.0142 (6)	0.0017 (6)	0.0035 (5)	−0.0004 (5)
N2	0.0231 (8)	0.0165 (7)	0.0222 (7)	0.0021 (6)	0.0080 (6)	0.0000 (6)
N3	0.0219 (9)	0.0358 (10)	0.0256 (8)	0.0091 (7)	0.0048 (7)	−0.0014 (7)
N4	0.0683 (15)	0.0228 (9)	0.0382 (11)	−0.0077 (9)	0.0102 (10)	−0.0057 (8)
C1	0.0204 (9)	0.0164 (8)	0.0134 (7)	0.0007 (7)	0.0032 (6)	−0.0038 (6)
C2	0.0172 (8)	0.0170 (8)	0.0141 (7)	0.0002 (7)	0.0031 (6)	−0.0016 (6)
C3	0.0222 (9)	0.0218 (9)	0.0156 (8)	0.0010 (7)	0.0072 (7)	−0.0015 (7)
C4	0.0249 (10)	0.0235 (9)	0.0161 (8)	0.0043 (7)	0.0036 (7)	0.0021 (7)
C5	0.0176 (9)	0.0221 (9)	0.0203 (8)	0.0027 (7)	0.0017 (7)	−0.0051 (7)
C6	0.0189 (9)	0.0268 (9)	0.0207 (8)	−0.0022 (7)	0.0074 (7)	−0.0020 (7)
C7	0.0214 (9)	0.0203 (9)	0.0167 (8)	−0.0016 (7)	0.0048 (7)	0.0010 (6)
C8	0.0166 (9)	0.0202 (9)	0.0213 (8)	0.0039 (7)	0.0026 (7)	−0.0008 (7)
C9	0.0240 (10)	0.0180 (8)	0.0194 (8)	0.0033 (7)	0.0003 (7)	0.0000 (7)
C10	0.0232 (10)	0.0223 (9)	0.0278 (9)	0.0021 (8)	0.0033 (8)	−0.0008 (7)
C11	0.0294 (11)	0.0216 (10)	0.0373 (11)	−0.0022 (8)	0.0050 (9)	0.0027 (8)
C12	0.0376 (12)	0.0219 (10)	0.0272 (10)	0.0044 (9)	−0.0024 (9)	−0.0031 (8)
C13	0.0516 (14)	0.0230 (10)	0.0230 (10)	0.0044 (9)	0.0114 (9)	−0.0005 (8)
C14	0.0381 (12)	0.0209 (9)	0.0246 (9)	0.0031 (8)	0.0100 (8)	0.0016 (7)
C15	0.0177 (9)	0.0158 (8)	0.0177 (8)	0.0011 (7)	0.0045 (7)	−0.0003 (6)
C16	0.0219 (9)	0.0211 (8)	0.0163 (8)	−0.0013 (7)	0.0056 (7)	0.0021 (7)
C17	0.0200 (9)	0.0234 (9)	0.0147 (8)	−0.0027 (7)	0.0067 (7)	−0.0019 (7)
C18	0.0144 (8)	0.0189 (8)	0.0166 (8)	0.0002 (7)	0.0035 (6)	−0.0010 (6)
C19	0.0177 (9)	0.0196 (8)	0.0152 (8)	0.0023 (7)	0.0039 (6)	0.0017 (6)
C20	0.0215 (9)	0.0198 (8)	0.0181 (8)	−0.0012 (7)	0.0098 (7)	−0.0008 (7)
C21	0.0232 (10)	0.0249 (9)	0.0221 (9)	0.0059 (8)	0.0022 (7)	−0.0018 (7)
C22	0.0265 (11)	0.0347 (11)	0.0333 (11)	−0.0057 (9)	0.0036 (9)	−0.0037 (9)
C23	0.0299 (11)	0.0181 (9)	0.0340 (10)	0.0057 (8)	0.0134 (9)	0.0020 (8)
C24	0.0483 (15)	0.0235 (11)	0.0517 (14)	0.0038 (10)	0.0199 (12)	0.0103 (10)
C25	0.0324 (12)	0.0353 (12)	0.0332 (11)	0.0149 (10)	0.0019 (9)	−0.0003 (9)
C26	0.113 (3)	0.0223 (11)	0.0298 (12)	−0.0021 (14)	0.0087 (14)	−0.0038 (9)

Zn1—Zn1i	2.9301 (4)	C10—C11	1.383 (3)
Zn1—O1	2.0224 (13)	C10—H10	0.93
Zn1—O2	2.0207 (13)	C11—H11	0.93
Zn1—O4	2.0459 (13)	C12—N4	1.369 (3)
Zn1—N1	2.0516 (14)	C12—C11	1.415 (3)
O1—C1	1.263 (2)	C12—C13	1.396 (3)
O2—C1i	1.272 (2)	C13—H13	0.93
O3—Zn1	2.0819 (14)	C14—C13	1.381 (3)
O3—C8	1.264 (2)	C14—H14	0.93
O4—C8i	1.276 (2)	C15—C16	1.384 (2)
O5—C20	1.240 (2)	C15—H15	0.93
O6—H61	0.94 (4)	C16—H16	0.93
O6—H62	0.96 (4)	C17—C16	1.384 (3)
N1—C15	1.344 (2)	C17—C18	1.392 (2)
N1—C19	1.343 (2)	C17—H17	0.93
N2—C20	1.336 (2)	C18—C19	1.385 (2)
N2—C21	1.471 (2)	C19—H19	0.93
N2—C23	1.475 (2)	C20—C18	1.505 (2)
N3—H3A	0.86	C21—C22	1.516 (3)
N4—C26	1.447 (3)	C21—H21A	0.97
N4—H4A	0.86	C21—H21B	0.97
C1—O2i	1.272 (2)	C22—H22A	0.96
C2—C1	1.480 (2)	C22—H22B	0.96
C2—C3	1.391 (2)	C22—H22C	0.96
C3—H3	0.93	C23—C24	1.515 (3)
C4—C3	1.381 (3)	C23—H23A	0.97
C4—C5	1.407 (3)	C23—H23B	0.97
C4—H4	0.93	C24—H24A	0.96
C5—N3	1.363 (2)	C24—H24B	0.96
C6—C5	1.410 (3)	C24—H24C	0.96
C6—H6	0.93	C25—N3	1.440 (3)
C7—C2	1.403 (2)	C25—H25A	0.96
C7—C6	1.371 (3)	C25—H25B	0.96
C7—H7	0.93	C25—H25C	0.96
C8—O4i	1.276 (2)	C26—H26A	0.96
C8—C9	1.479 (2)	C26—H26B	0.96
C9—C10	1.394 (3)	C26—H26C	0.96
C9—C14	1.400 (3)
O1—Zn1—Zn1i	73.77 (4)	C12—C11—H11	119.7
O1—Zn1—O3	86.65 (6)	N4—C12—C11	118.8 (2)
O1—Zn1—O4	88.23 (6)	N4—C12—C13	122.8 (2)
O1—Zn1—N1	94.78 (5)	C13—C12—C11	118.43 (19)
O2—Zn1—Zn1i	86.29 (4)	C12—C13—H13	119.9
O2—Zn1—O1	159.63 (5)	C14—C13—C12	120.18 (19)
O2—Zn1—O3	90.72 (6)	C14—C13—H13	119.9
O2—Zn1—O4	87.59 (5)	C9—C14—H14	119.2
O2—Zn1—N1	105.52 (5)	C13—C14—C9	121.57 (19)
O3—Zn1—Zn1i	70.66 (4)	C13—C14—H14	119.2
O4—Zn1—Zn1i	89.93 (4)	N1—C15—C16	122.34 (16)
O4—Zn1—O3	160.59 (5)	N1—C15—H15	118.8
O4—Zn1—N1	106.76 (6)	C16—C15—H15	118.8
N1—Zn1—Zn1i	159.67 (4)	C15—C16—H16	120.5
N1—Zn1—O3	92.33 (6)	C17—C16—C15	119.04 (16)
C1—O1—Zn1	135.44 (13)	C17—C16—H16	120.5
C1i—O2—Zn1	119.36 (11)	C16—C17—C18	119.00 (16)
C8—O3—Zn1	139.69 (12)	C16—C17—H17	120.5
C8i—O4—Zn1	115.95 (12)	C18—C17—H17	120.5
H62—O6—H61	103 (3)	C17—C18—C20	120.11 (15)
C15—N1—Zn1	125.96 (12)	C19—C18—C17	118.48 (16)
C19—N1—Zn1	115.38 (11)	C19—C18—C20	120.80 (15)
C19—N1—C15	118.45 (15)	N1—C19—C18	122.65 (16)
C20—N2—C21	124.58 (15)	N1—C19—H19	118.7
C20—N2—C23	118.32 (16)	C18—C19—H19	118.7
C21—N2—C23	117.04 (16)	O5—C20—N2	122.74 (17)
C5—N3—C25	122.12 (17)	O5—C20—C18	117.80 (17)
C5—N3—H3A	118.9	N2—C20—C18	119.45 (16)
C25—N3—H3A	118.9	N2—C21—C22	111.97 (16)
C12—N4—C26	123.4 (2)	N2—C21—H21A	109.2
C12—N4—H4A	118.3	N2—C21—H21B	109.2
C26—N4—H4A	118.3	C22—C21—H21A	109.2
O1—C1—O2i	124.19 (17)	C22—C21—H21B	109.2
O1—C1—C2	117.03 (15)	H21A—C21—H21B	107.9
O2i—C1—C2	118.78 (15)	C21—C22—H22A	109.5
C3—C2—C1	122.21 (16)	C21—C22—H22B	109.5
C3—C2—C7	118.19 (16)	C21—C22—H22C	109.5
C7—C2—C1	119.55 (15)	H22A—C22—H22B	109.5
C2—C3—H3	119.5	H22A—C22—H22C	109.5
C4—C3—C2	121.08 (17)	H22B—C22—H22C	109.5
C4—C3—H3	119.5	N2—C23—C24	111.91 (16)
C3—C4—C5	120.62 (17)	N2—C23—H23A	109.2
C3—C4—H4	119.7	N2—C23—H23B	109.2
C5—C4—H4	119.7	C24—C23—H23A	109.2
N3—C5—C4	121.78 (17)	C24—C23—H23B	109.2
N3—C5—C6	119.95 (17)	H23A—C23—H23B	107.9
C4—C5—C6	118.26 (17)	C23—C24—H24A	109.5
C5—C6—H6	119.9	C23—C24—H24B	109.5
C7—C6—C5	120.25 (17)	C23—C24—H24C	109.5
C7—C6—H6	119.9	H24A—C24—H24B	109.5
C2—C7—H7	119.2	H24A—C24—H24C	109.5
C6—C7—C2	121.56 (17)	H24B—C24—H24C	109.5
C6—C7—H7	119.2	N3—C25—H25A	109.5
O3—C8—O4i	123.76 (17)	N3—C25—H25B	109.5
O3—C8—C9	117.69 (16)	N3—C25—H25C	109.5
O4i—C8—C9	118.55 (16)	H25A—C25—H25B	109.5
C10—C9—C8	121.59 (17)	H25A—C25—H25C	109.5
C10—C9—C14	118.31 (18)	H25B—C25—H25C	109.5
C14—C9—C8	120.10 (17)	N4—C26—H26A	109.5
C9—C10—H10	119.6	N4—C26—H26B	109.5
C11—C10—C9	120.71 (19)	N4—C26—H26C	109.5
C11—C10—H10	119.6	H26A—C26—H26B	109.5
C10—C11—C12	120.6 (2)	H26A—C26—H26C	109.5
C10—C11—H11	119.7	H26B—C26—H26C	109.5
Zn1i—Zn1—O1—C1	−10.58 (16)	C20—N2—C23—C24	86.7 (2)
O2—Zn1—O1—C1	−22.8 (3)	C21—N2—C23—C24	−96.1 (2)
O3—Zn1—O1—C1	60.23 (17)	C3—C2—C1—O1	175.07 (16)
O4—Zn1—O1—C1	−101.03 (17)	C3—C2—C1—O2i	−4.9 (3)
N1—Zn1—O1—C1	152.30 (17)	C7—C2—C1—O1	−2.3 (2)
Zn1i—Zn1—O2—C1i	1.39 (12)	C7—C2—C1—O2i	177.77 (16)
O1—Zn1—O2—C1i	13.1 (2)	C1—C2—C3—C4	−176.37 (17)
O3—Zn1—O2—C1i	−69.17 (13)	C7—C2—C3—C4	1.0 (3)
O4—Zn1—O2—C1i	91.48 (13)	C3—C4—C5—N3	177.78 (18)
N1—Zn1—O2—C1i	−161.79 (12)	C5—C4—C3—C2	−0.3 (3)
Zn1i—Zn1—O4—C8i	−0.04 (12)	C3—C4—C5—C6	−1.3 (3)
O1—Zn1—O4—C8i	73.72 (13)	C4—C5—N3—C25	5.1 (3)
O2—Zn1—O4—C8i	−86.33 (13)	C6—C5—N3—C25	−175.77 (19)
O3—Zn1—O4—C8i	−1.0 (2)	C7—C6—C5—N3	−176.90 (18)
N1—Zn1—O4—C8i	168.18 (12)	C7—C6—C5—C4	2.2 (3)
Zn1i—Zn1—N1—C15	−165.91 (10)	C6—C7—C2—C1	177.35 (17)
Zn1i—Zn1—N1—C19	8.7 (2)	C6—C7—C2—C3	−0.1 (3)
O1—Zn1—N1—C15	139.65 (15)	C2—C7—C6—C5	−1.5 (3)
O1—Zn1—N1—C19	−45.76 (13)	O3—C8—C9—C10	163.73 (18)
O2—Zn1—N1—C15	−42.11 (16)	O3—C8—C9—C14	−15.5 (3)
O2—Zn1—N1—C19	132.48 (12)	O4i—C8—C9—C10	−15.9 (3)
O3—Zn1—N1—C15	−133.51 (15)	O4i—C8—C9—C14	164.81 (18)
O3—Zn1—N1—C19	41.08 (13)	C8—C9—C10—C11	−175.97 (18)
O4—Zn1—N1—C15	50.06 (15)	C14—C9—C10—C11	3.3 (3)
O4—Zn1—N1—C19	−135.35 (12)	C8—C9—C14—C13	177.63 (19)
Zn1—O1—C1—O2i	13.4 (3)	C10—C9—C14—C13	−1.6 (3)
Zn1—O1—C1—C2	−166.52 (12)	C9—C10—C11—C12	−1.1 (3)
C8—O3—Zn1—Zn1i	1.03 (19)	C13—C12—N4—C26	−0.3 (4)
C8—O3—Zn1—O1	−72.9 (2)	C11—C12—N4—C26	−180.0 (2)
C8—O3—Zn1—O2	86.8 (2)	N4—C12—C11—C10	176.8 (2)
C8—O3—Zn1—O4	2.1 (3)	C13—C12—C11—C10	−2.9 (3)
C8—O3—Zn1—N1	−167.6 (2)	N4—C12—C13—C14	−175.2 (2)
Zn1—O3—C8—O4i	−1.4 (3)	C11—C12—C13—C14	4.5 (3)
Zn1—O3—C8—C9	178.98 (14)	C9—C14—C13—C12	−2.3 (3)
Zn1—N1—C15—C16	174.78 (13)	N1—C15—C16—C17	−1.9 (3)
C19—N1—C15—C16	0.3 (3)	C18—C17—C16—C15	1.9 (3)
Zn1—N1—C19—C18	−173.78 (14)	C16—C17—C18—C19	−0.4 (3)
C15—N1—C19—C18	1.2 (3)	C16—C17—C18—C20	−171.52 (17)
C21—N2—C20—O5	−176.81 (17)	C17—C18—C19—N1	−1.2 (3)
C21—N2—C20—C18	3.5 (3)	C20—C18—C19—N1	169.86 (16)
C23—N2—C20—O5	0.2 (3)	O5—C20—C18—C17	67.7 (2)
C23—N2—C20—C18	−179.51 (15)	O5—C20—C18—C19	−103.2 (2)
C20—N2—C21—C22	97.4 (2)	N2—C20—C18—C17	−112.63 (19)
C23—N2—C21—C22	−79.6 (2)	N2—C20—C18—C19	76.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O6ii	0.86	2.50	3.105 (3)	128
N4—H4A···O6iii	0.86	2.07	2.922 (3)	171
O6—H61···O4iv	0.93 (4)	2.07 (4)	2.875 (2)	143 (3)
O6—H61···O2iv	0.93 (4)	2.37 (4)	3.117 (2)	137 (3)
O6—H62···O5v	0.96 (4)	1.81 (4)	2.741 (2)	162 (3)

Table 1

Selected bond lengths (Å)

Zn1—O1	2.0224 (13)
Zn1—O2	2.0207 (13)
Zn1—O3	2.0819 (14)
Zn1—O4	2.0459 (13)
Zn1—N1	2.0516 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O6i	0.86	2.50	3.105 (3)	128
N4—H4A⋯O6ii	0.86	2.07	2.922 (3)	171
O6—H61⋯O4iii	0.93 (4)	2.07 (4)	2.875 (2)	143 (3)
O6—H61⋯O2iii	0.93 (4)	2.37 (4)	3.117 (2)	137 (3)
O6—H62⋯O5iv	0.96 (4)	1.81 (4)	2.741 (2)	162 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .